The last time Tracy McGrady wore a Raptors uniform Y2K was just a few months old. It has been more than a decade – with stops in Orlando, Houston, New York, and Atlanta along the way – but every time ‘T-Mac’ comes back to Toronto, he is showered with boos.

Some fans accept the fact that McGrady left T.O. for the opportunity to lead his own team – close to home – and escape the shadow of cousin, Vince Carter. Others won’t forgive him for allegedly giving management in Toronto false hope that he’d re-sign; quickly walking away from the ‘Bring Back T-Mac’ signs that filled the Air Canada Centre in the spring of 2000. But few can’t help to have that ‘What if’ moment when reminiscing about the Raptors’ brief moment in history; when two young stars – Carter and McGrady – could have had the opportunity to dominate a conference together, surrounded by solid veterans and hard-nosed teammates like Charles Oakley, Antonio Davis, Alvin Williams and more.

Kobe Bryant once said that if McGrady had stayed in Toronto, there was no doubt in his mind that the Raptors would have beaten the Philadelphia 76ers in 2001 (when Carter’s Game 7 buzzer-beater rimmed out and the Sixers went on to the Eastern Conference Finals and then the NBA Finals (after beating Milwaukee); eventually losing to Los Angeles). Bryant said the Lakers and Raptors could have been squaring-off in the Finals for years to come.

On our post-game show last night – after the Hawks blew out the Raptors at the ACC – Paul Jones and I asked McGrady if he thought Bryant’s assessment was correct and if he allows himself to have those same ‘What if’ moments about staying in Toronto.

“All the time,” he said. “All the time.”

“You HAD to bring up that question,” he joked. But then he continued and confirmed what Bryant and many Raptors fans have felt for years.

“I look back on how good I was when I left here and played in Orlando. I look at how great Vince was. I look at that team that they had when they faced Philly. What was is it, Game 7? When (Carter) missed that shot in the corner? There’s no doubt if I was part of that team what we could have done. But that’s hindsight looking back man, ya know?”

Nobody can say for sure what would have happened to Toronto if McGrady had indeed stayed with the Raptors. Finances, coaches, personnel, trades, drafts, and so many more intangibles would have been different. The path and the history of the organization – good or bad – would have been totally altered from where it is today. But as T-Mac said, that’s hindsight.

Looking forward, the Raptors are trying to figure out what they have right now. Do they have a young core to build around with the likes of DeMar DeRozan, Ed Davis, Jonas Valanciunas and Andrea Bargnani? If the answer to that question is ‘yes’ and Toronto starts to build a winner and a contender in the NBA, the hope is that the only team that’s north of the border in the Association will start to attract top talent again. And even McGrady said he’d look at the Raptors again.

“Why not,” he told us on Sportsnet 590 the FAN. “This is a great city. It’s a great organization.”

“Unfortunately, I had to make a career decision for myself (back in 2000) and there’s no way I could have turned down being back home in Orlando. But at the tail-end of my career if they build something here? Absolutely. I don’t see why not. It’s just a great atmosphere to play basketball, (there’s) great fan support and it’s just a great city to live in.”

When asked if he’d be welcomed back by the fans, McGrady smiled and joked: “Is it ‘once a Raptor, always a Raptor?’ Is that a true?”